Family-friendly holiday rentals in Oakville

4.93 out of 5 average rating, 211 reviews

An open studio layout displays a cozy sleeping area alongside a well-equipped kitchen. Light grey walls enhance the space, while two bedside lamps provide soft illumination. In-suite laundry is visible next to the kitchen, and a welcoming couch adds comfort to the environment.

Guesthouse in Oakville

Self Contained Luxury Studio Coach House

Your Perfect Home Away from Home! This immaculate, private studio with a separate entrance is designed for comfort and convenience. Nestled in a peaceful suburb yet centrally located near major highways, it offers walking access to restaurants, grocery stores, and a park. Thoughtfully furnished, it’s cozy in winter, cool in summer, and fully equipped for a hassle-free stay. Guests love the warm ambiance, calling it a truly special experience. Come see why our coach house is the perfect getaway!

Guest suite in Mississauga

A spacious studio is showcased, featuring a large bed adorned with textured pillows. A comfy chair and small table are positioned beside the bed. The modern kitchenette is visible in the background, equipped with essential appliances and stylish cabinetry. Soft lighting enhances the overall ambiance.

4.95 out of 5 average rating, 111 reviews

Luxurious Private Studio Portion (Basement)

Immerse your self in to the luxury and feel immediate sense of serenity and peace in this unique studio. Designer looks with upgraded decors and finish. Thoughtfully designed Bathroom - LED Makeup mirror lights. Equipped with Bosch microwave, Nespresso, romantically cozy Napoleon fireplace, cooktop, minifridge, utensils.. Airport 10, Toronto DT 30, Niagara 90, Malls & many restaurants at 2 mins drive. Everything maintained in immaculate condition and waiting your arrival. NO SMOKING/PETS

4.98 out of 5 average rating, 105 reviews

The exterior of a two-level apartment is shown, featuring a wooden deck accessible by stairs. A light brick facade complements large windows, while potted flowers add color to the entrance. Surrounding greenery enhances the inviting atmosphere of the building.

Apartment in Mississauga

Cozy apartment with Free Parking !

Centrally located prime location near buss, highway, parks, shopping, groceries, restaurants and movie theater. Minutes from major highway QEW, 35 min drive to Toronto and Airport. It is spacious, 2 level split apartment. Washroom and bedroom on the upper level. TV & Kitchen on the lower level. Kitchen is equipped with fridge, pots, microwave, toaster, air fryer, utensils, coffee maker. Smart TV, Netflix, Wifi, Parking, Private lawndry are all included. Not permitted: pets, smoking, parties.

A contemporary kitchen is highlighted by sleek cabinetry and a spacious island with bar seating. Stainless steel appliances, including a refrigerator and oven, are visible. Soft lighting enhances the modern design, and a mirror reflects the lush greenery in the corner, adding depth to the space.

4.96 out of 5 average rating, 116 reviews

Condo Style Basement in Oakville (Walk Up)

Looking for a cozy and comfortable place to stay during your next vacation or business trip? This spacious and stylish Airbnb accommodates up to 6 guests! Our beautiful space features everything you need to feel right at home! This condo style basement apartment is located in Oakville, one of Ontario’s most desirable neighbourhoods. 2 bedrooms with walk in closets 2 full bathrooms Sofa-come bed Contemporary chef kitchen (including utensils ) TV with Disney Plus and Netflix Dryer and washers

A cozy living area features a light grey sofa and a plush dark blue chair, arranged around a small white TV stand facing a flat screen television. A decorative rug covers the floor, and a dining table with two chairs is positioned nearby, complemented by a vase of flowers.

4.99 out of 5 average rating, 139 reviews

Bright, Spacious, Quiet 2 bedroom - Licensed

Quiet family neighborhood great for professionals, couples or family. Spacious and cozy home away from home. You control heat and cooling fan. Sound dampening so natural noises are minimized, not eliminated. 1 queen and 1 double bed. Two desks for computer work. Extra seating. Fast WiFi! Full kitchen. Bathroom with shower and bathtub. Close to highways, hospital, recreation centers, playgrounds, shopping, schools and college. All registered guests may be asked to provide ID upon request.

4.94 out of 5 average rating, 156 reviews

An open-plan living area is visible, featuring a modern kitchen equipped with stainless steel appliances, including an oven and refrigerator. A cozy grey sofa is positioned in front of a wooden coffee table. A circular dining table is set against a bright window, enhancing the space.

Apartment in Milton

Luxury Guest Suite

Welcome to our cozy basement apartment! This modern Airbnb is located in a peaceful residential neighborhood 40 min drive from Toronto downtown and an hour from Niagara Falls. The well-lit space features a comfortable queen-sized bed, ample storage in the spacious closet, and a beautifully designed interior with natural light flooding through large windows. Note: We have 2 single folding matresses available to place on the floor in the living room. Extra linen and pillows are provided.

Superhost

A spacious common area features a comfortable dark sectional sofa with a soft throw blanket draped over it. A sleek desk with a chair is positioned nearby, complemented by decorative wall art. The warm wooden flooring contributes to a cozy and inviting atmosphere.

Home in Clarkson

4.77 out of 5 average rating, 196 reviews

Private 2Bed Basement Apt |Self-Check with Kitchn

Modern, entirely private and super spacious 2 bed+ bath basement apartment (over 1200 sq ft). Less than a 2 minute drive to the QEW and a 5 minute drive to one of Mississauga's hottest entertainment plaza (Demetres cafe, Cineplex, Dave & Busters, Indoor skydiving, Scadabush, KB Sushi and more!) Hosts a kitchen (with fridge, microwave, coffee machine/kettle, toaster etc.) and common space with 42" TV, Netflix app and high speed Wifi. Separate entrance and free parking (1 car) included.

4.9 out of 5 average rating, 115 reviews

A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.

Home in West Oakville

Large Luxury Villa with Swim Spa! Near downtown!

Forget your worries in this spacious, serene and unique house! Large backyard with a Swim Spa to enjoy! Backyard filled with fire places! 6 Bedroom, 7 beds, 4 full baths, 4 offices, 3 family rooms, 9 TV, equipped kitchen, patio, board games, BBQ grill, fire place, Tesla charger. Quiet yet central from downtown Oakville, highways, groceries, shopping, bars, restaurants, cafe's and much more! Always professionally cleaned. For elderly guests a bedroom and full bath is on ground floor.

4.88 out of 5 average rating, 267 reviews

A bright and modern space features a cozy red sofa, complemented by a round coffee table resting on a textured rug. A spacious bed is seen in the background, with natural light filtering through a window, illuminating the soft bedding.

Apartment in Mississauga

One bedroom Apt. ( 2 storeys unit ) in Mississauga

You will love this one bedroom self-contained 2 storeys unit with separated entrance near Square One mall in downtown Mississauga and 15 minutes to Pearson Airport, easy access to highway 401 and highway 403 and close to all amenities. Modern design bright & spacious with beautiful and private view. Enjoy with free high speed Wi-Fi & 43" tv Netflix available, one parking spot side by side , all included. Quiet neighborhood. - Sorry No party, No smoking, Filming nor Event Stay.

Superhost

A modern studio space is captured featuring a cozy bed adorned with white linen and decorative pillows. A sleek stainless steel refrigerator is positioned nearby, alongside a small wooden table with a potted plant. Natural light filters through a window, enhancing the inviting atmosphere.

4.79 out of 5 average rating, 139 reviews

Cozy Modern Studio in Oakville | Free Parking

Welcome to your perfect retreat - an oasis for 1-2 guests seeking ultimate comfort. Enjoy seamless connectivity with WiFi, Netflix, and a luxurious Queen bed. Experience the essence of home in our inviting, modern basement studio. With a full kitchenette, in-unit laundry, and lots of storage. This modern unit is ideally situated in a serene, safe neighborhood in Oakville, steps from public transit, close to various amenities like restaurants, malls and trails

Dome in Aldershot Central

4.96 out of 5 average rating, 160 reviews

Winter Escape Tropical Dome! Animal Lovers Dream

Jungle Dome on a farm in Burlington! Enjoy a tropical stay in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed to be a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can feed and interact with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

4.96 out of 5 average rating, 114 reviews

A modern kitchen features sleek white cabinetry and a large island with seating for four. Stainless steel appliances are visible, including a refrigerator and microwave. Bright lighting fixtures hang above the island, and a small green plant adds a touch of freshness to the countertop.

Home in Oakville

Elegant 2BR townhouse condo in central Oakville

Enjoy your stay in this elegant, clean, and fully equipped two bedroom and two-bathroom condo townhouse. Centrally located in Oakville and within walking distance to shops, restaurants, and parks. Beautiful upscale building in a quiet and safe neighborhood with large terrace overlooking a mature tree lined street. Abundant walking trails nearby for you to explore and enjoy. Easy access to highway 407, 403, QEW and Trafalgar GO Station.

Popular amenities for Oakville family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Holiday home in Stoney Creek

4.87 out of 5 average rating, 151 reviews

The Waterfront Oasis – Views, Firepit & Hot Tub

Villa in Aldershot Central

The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.

4.96 out of 5 average rating, 157 reviews

Waterfront Hillside Villa

4.87 out of 5 average rating, 196 reviews

A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.

Condo in Mississauga

Beautiful Penthouse with Breathtaking View

4.98 out of 5 average rating, 596 reviews

A vibrant sunset is captured with layers of orange, red, and yellow hues across the sky. Silhouetted trees and foliage frame the image, creating a contrasting foreground against the colorful backdrop.

Guest suite in Hamilton

Country Getaway in Puslinch

4.94 out of 5 average rating, 151 reviews

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Apartment in Mississauga

Luxury Stay w/phenomenal view!

4.93 out of 5 average rating, 278 reviews

An open concept living area showcases a spacious seating arrangement with a neutral-colored sofa, paired with a wooden dining table. Exposed wooden beams and a rustic stone wall add character to the space, with natural light flowing through large windows.

Barn in Hamilton

The Barn-Fieldstone Suite

4.84 out of 5 average rating, 292 reviews

A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.

Condo in Mississauga

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

4.74 out of 5 average rating, 136 reviews

An aerial view showcases a secluded backyard featuring a blue swimming pool surrounded by green trees. Umbrellas and seating areas are visible adjacent to the pool, and a separate structure can be seen nearby, adding to the serene outdoor space.

Bungalow in Shoreacres

Sleeps 12 ADULT private hot tub pool Walk to Lake

Family- and pet-friendly home rentals

Superhost

The entrance is framed by two large pots filled with vibrant orange flowers, positioned on either side of the door. A welcome mat lies in front of the door, with a decorative broom leaning against the wall, complemented by a brick facade.

Apartment in Hamilton

4.89 out of 5 average rating, 123 reviews

THE NEST - Cuddle Up In This Quaint Retreat

4.94 out of 5 average rating, 201 reviews

A doorway opens to a private deck featuring two wooden chairs with white cushions and a small table between them. The view showcases lush greenery and rolling farmland, under a clear sky.

Guesthouse in Lincoln

Little Blue Barn on the Bench

4.82 out of 5 average rating, 280 reviews

A spacious living area features a dark leather sofa and a wooden coffee table at its center. A framed winter landscape hangs on the wall, while two lamps provide soft lighting. In the background, a dining counter with stools is visible, leading to the kitchen.

Townhouse in Burlington

The Best of Downtown Burlington - Safe & Clean

4.94 out of 5 average rating, 274 reviews

A single-story cottage features a wooden exterior with large windows and a black roof. A path of gravel leads to the entrance, which is framed by greenery and stones. Surrounding the building, the landscape showcases well-maintained grass and a young tree.

Farm stay in Hamilton

Somerset Cottage at West Avenue Cider House

4.89 out of 5 average rating, 211 reviews

A modern kitchen area is displayed, featuring white cabinetry and stainless steel appliances. A sleek, circular coffee table is positioned in front of a comfortable white sofa, with light hardwood flooring throughout. Natural light illuminates the space from a nearby window, enhancing the contemporary décor.

Home in Mississauga

Private 1-br Apartment: Your Secluded Getaway!

4.95 out of 5 average rating, 108 reviews

A spacious living area is presented with a comfortable gray sectional couch and a round wooden coffee table. A large TV is mounted on a textured wall, while a piece of artwork depicting waves adds character to the room. A guitar rests nearby, complementing the inviting atmosphere.

Guest suite in Hamilton

Adorable 1-Bedroom Basement Apartment in Hamilton

The kitchen area includes white cabinetry and a stainless steel stove. A dining table with dark wooden chairs is positioned in front of a wall-mounted TV. A patterned rug covers the tiled floor, while a doorway leads to another room.

4.83 out of 5 average rating, 120 reviews

Cozy basement apartment in the heart of Oakville

Guesthouse in Halton Hills

A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.

4.92 out of 5 average rating, 158 reviews

The Clayhill Bunkie

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 103 reviews

Five alpacas are seen walking across a grassy area in front of a large, restored barn. The barn features a dark roof and wooden siding, with a door visible on the lower level. A clear blue sky and scattered clouds provide a bright backdrop.

Farm stay in Caledonia

Alpaca farm stay and bunkie getaway.

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

4.92 out of 5 average rating, 812 reviews

Hot Tub & Cozy Fireplace - Headwaters Retreat

Guest suite in Mississauga

A well-lit bedroom features a spacious bed with crisp white linens. Two wooden nightstands with lamps are positioned on either side, complemented by a wooden storage chest at the foot of the bed. Soft carpet blankets the floor, creating a cozy atmosphere.

4.97 out of 5 average rating, 116 reviews

The Homelands Suite, 2 Bedroom with Pool.

5 out of 5 average rating, 126 reviews

A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.

Condo in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

4.84 out of 5 average rating, 185 reviews

A scenic lake view is presented, featuring a wooden bench positioned on a grassy area beside the water. The sun reflects off the lake's surface, and a clear blue sky is adorned with a few fluffy clouds, creating a serene atmosphere.

Guest suite in Bronte

Stylish Basement Hideaway*1 BR Suite*Near Lake

4.96 out of 5 average rating, 137 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guesthouse in Erin

The Captain's Cottage at Willow Pond

Apartment in Oakwood Village

A spacious living room is presented with a neutral-colored sectional sofa adorned with yellow accent pillows. A small glass side table complements the seating area, while a patterned area rug adds texture to the floor. Natural light enters through a window placed above the sofa.

4.85 out of 5 average rating, 102 reviews

Bright, spacious luxury basement apartment